Oh man, the simplest thing in the world

[Huffman]

I couldn't get it in. Seriously, she was so tight that I couldn't get it in. And yes she was wet, I made sure of it! But it just wouldn't go in. Also after putting on the condom I was only medium-hard so that didn't help either. She wasn't even a virgin but said it's because she "hadn't done it in a while". We tried a couple of times but ended up not doing it... what could I have done!?

 

[Strelok]

The problem is that "medium-hard" ****,you need something hard even to stick the butter.
Anyway sometime it happened to me too,the condom give a negative mental impact and disturb erection,hard to explain.

 

[Teflon_Mcgee]

Ditto what Strelok said.

That being said, you could have fingered her to loosen her up a little. You'd be amazed how much more you could fit in there if you work it for a few minutes.

 

[Mr.Positive]

One of the few one night stands I've had was with a gal like that. You've got to be rock hard. What I did, was question myself, is this going to fit? Yes, she was that tiny.

I didn't want to try forcing it, so I guided her on top and let her see what she could do. She got it in maybe an inch or two. I lasted about a minute..haha. Round two was a bit better, however some gals are just too tight.

So my recommendation, is make sure you are hard enough, and guide her on top of you and enjoy the ride.